Substituted 1-amino-3-phenyluracil derivatives, their preparation and their use as herbicides

ABSTRACT

PCT No. PCT/EP96/03693 Sec. 371 Date Feb. 25, 1998 Sec. 102(e) Date Feb. 25, 1998 PCT Filed Aug. 22, 1996 PCT Pub. No. WO97/09319 PCT Pub. Date Mar. 13, 1997The invention relates to novel substituted aminouracils of the general formula (I) in which R1, R2, R3, R4, R5, R6, R7 and R8 are each as defined in the claims, to the preparation thereof and to their use as herbicides.

The invention relates to novel substituted aminouracils, to thepreparation thereof and to their use as herbicides.

Certain substituted uracils are known to have herbicidal properties (cf.EP 408382/U.S. Pat. No. 5,084,084/U.S. Pat. No. 5,127,935/U.S. Pat. No.5,154,755/EP 563384/EP 648749/WO 91/00278/U.S. Pat. No. 4,979,982/U.S.Pat. No. 5,169,430). However, these compounds are of no particularimportance.

This invention, accordingly, provides the novel substituted aminouracilsof the general formula (I) ##STR2## in which

R¹ represents hydrogen, cyano or halogen,

R² represents cyano or thiocarbamoyl,

R³ represents hydrogen or represents a respectively optionallysubstituted radical from the group consisting of alkyl, alkylcarbonyl,alkenyl, alkenylcarbonyl, alkinyl, alkinylcarbonyl, cycloalkyl,cycloalkylcarbonyl, cycloalkylalkyl, cycloalkylalkylcarbonyl,arylcarbonyl, arylalkylcarbonyl and heterocyclylcarbonyl,

R⁴ represents hydrogen or represents a respectively optionallysubstituted radical from the group consisting of alkyl, alkylcarbonyl,alkenyl, alkenylcarbonyl, alkinyl, alkinylcarbonyl, cycloalkyl,cycloalkylcarbonyl, cycloalkylalkyl, cycloalkylalkylcarbonyl,arylcarbonyl, arylalkylcarbonyl and heterocyclylcarbonyl, or togetherwith R³ represents respectively optionally substituted alkanediyl,oxoalkanediyl or dioxoalkanediyl,

R⁵ represents hydrogen, halogen or respectively optionally substitutedalkyl or alkoxy,

R⁶ represents optionally substituted alkyl,

R⁷ represents hydrogen or represents a respectively optionallysubstituted radical from the group consisting of alkyl, alkenyl andalkinyl, and

R⁸ represents hydrogen or represents a respectively optionallysubstituted radical from the group consisting of alkyl, alkenyl andalkinyl.

The novel substituted aminouracils of the general formula (I) areobtained when aminouracils of the general formula (II) ##STR3## in which

R¹, R², R⁵, R⁶, R⁷ and R⁸ are each as defined above and

Z represents optionally substituted alkylsulphonylamino or the groupingNR³ R⁴, where R³ and R⁴ are each as defined above,

are reacted with alkylating or acylating agents of the general formulae(III), (IV), (V) or (VI)

    X--R.sup.3                                                 (III)

    R.sup.3 --CO--O--CO--R.sup.3                               (IV)

    X--R.sup.4                                                 (V)

    R.sup.4 --CO--O--CO--R.sup.4                               (VI)

in which

R³ and R⁴ are each as defined above,

if appropriate in the presence of a reaction auxiliary and ifappropriate in the presence of a diluent.

The compounds of the general formula (I) can be converted byconventional methods into other compounds of the general formula (I)according to the definition above, for example by deacylation withammonium acetate/glacial acetic acid (R³ /R⁴ : --CO--CH₃ →H) or by theaddition of hydrogen sulphide (R² : CN→CSNH₂).

The novel substituted aminouracils of the general formula (I) havestrong herbicidal properties.

In the definitions, the saturated or unsaturated hydrocarbon chains,such as alkyl, alkenyl or alkinyl, are in each case straight-chain orbranched.

Halogen generally represents fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine, in particular fluorine orchlorine.

The invention preferably provides compounds of the formula (I) in which

R¹ represents hydrogen, cyano, fluorine or chlorine,

R² represents cyano or thiocarbamoyl,

R³ represents hydrogen or represents respectively optionally cyano-,carboxyl-, fluorine-, chlorine-, bromine-, C₁ -C₄ -alkoxy-, C₁ -C₄-alkyl-carbonyl- or C₁ -C₄ -alkoxy-carbonyl-substituted alkyl,alkylcarbonyl, alkenyl, alkenylcarbonyl, alkinyl or alkinylcarbonylhaving in each case up to 10 carbon atoms in the alkyl, alkenyl oralkinyl moieties,

R³ furthermore represents respectively optionally cyano-, carboxyl-,fluorine-, chlorine-, bromine-, C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy-, C₁ -C₄-alkyl-carbonyl- or C₁ -C₄ -alkoxy-carbonyl-substituted cycloalkyl,cycloalkylcarbonyl, cycloalkylalkyl or cycloalkylalkylcarbonyl having ineach case 3 to 8 carbon atoms in the cycloalkyl moiety and optionally upto 4 carbon atoms in the alkyl moiety,

R³ furthermore represents arylcarbonyl or arylalkylcarbonyl having 6 or10 carbon atoms in the aryl moiety and optionally up to 4 carbon atomsin the alkyl moiety, each of the arylcarbonyl or arylalkylcarbonylradicals optionally being substituted by cyano, carboxyl, nitro,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C₁ -C₄ -alkyl,C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄-alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl (eachof which is optionally substituted by fluorine and/or chlorine), byphenyl, phenoxy or phenylthio (each of which is optionally substitutedby fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyland/or trifluoromethoxy),

R³ furthermore represents substituted furylcarbonyl,tetrahydrofurylcarbonyl, thienylcarbonyl, tetrahydrothienylcarbonyl,oxazolylcarbonyl, isoxazolylcarbonyl, thiazolylcarbonyl,oxadiazolylcarbonyl, thiadiazolylcarbonyl, pyrazolylcarbonyl,pyridinylcarbonyl or pyrimidinylcarbonyl, each of which is optionallysubstituted by cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine,chlorine, bromine, by C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonylor C₁ -C₄ -alkoxy-carbonyl (each of which is optionally substituted byfluorine and/or chlorine), by phenyl, phenoxy or phenylthio (each ofwhich is optionally substituted by fluorine, chlorine, bromine, cyano,methyl, methoxy, trifluoromethyl and/or trifluoromethoxy),

R⁴ represents hydrogen or represents respectively optionally cyano-,carboxyl-, fluorine-, chlorine-, bromine-, C₁ -C₄ -alkoxy-, C₁ -C₄-alkyl-carbonyl- or C₁ -C₄ -alkoxy-carbonyl-substituted alkyl,alkylcarbonyl, alkenyl, alkenylcarbonyl, alkinyl or alkinylcarbonylhaving in each case up to 10 carbon atoms in the alkyl, alkenyl oralkinyl moieties,

R⁴ furthermore represents respectively optionally cyano-, carboxyl-,fluorine-, chlorine-, bromine-, C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy-, C₁ -C₄-alkyl-carbonyl- or C₁ -C₄ -alkoxy-carbonyl-substituted cycloalkyl,cycloalkylcarbonyl, cycloalkylalkyl or cycloalkylalkylcarbonyl having ineach case 3 to 8 carbon atoms in the cycloalkyl moiety and optionally upto 4 carbon atoms in the alkyl moiety,

R⁴ furthermore represents arylcarbonyl or arylalkylcarbonyl having 6 or10 carbon atoms in the aryl moiety and optionally up to 4 carbon atomsin the alkyl moiety, each of the arylcarbonyl or arylalkylcarbonylradicals optionally being substituted by cyano, carboxyl, nitro,carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C₁ -C₄ -alkyl,C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄-alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl or C₁ -C₄ -alkoxy-carbonyl (eachof which is optionally substituted by fluorine and/or chlorine), byphenyl, phenoxy or phenylthio (each of which is optionally substitutedby fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyland/or trifluoromethoxy),

R⁴ furthermore represents furylcarbonyl, tetrahydrofurylcarbonyl,thienylcarbonyl, tetrahydrothienylcarbonyl, oxazolylcarbonyl,isoxazolylcarbonyl, thiazolylcarbonyl, oxadiazolylcarbonyl,thiadiazolylcarbonyl, pyrazolylcarbonyl, pyridinylcarbonyl orpyrimidinylcarbonyl, each of which is optionally substituted by cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C₁-C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl,C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl or C₁ -C₄-alkoxy-carbonyl (each of which is optionally substituted by fluorineand/or chlorine), by phenyl, phenoxy or phenylthio (each of which isoptionally substituted by fluorine, chlorine, bromine, cyano, methyl,methoxy, trifluoromethyl and/or trifluoromethoxy),

R⁴ together with R³ represents respectively optionally fluorine-,chlorine-, bromine-, C₁ -C₄ -alkyl- or C₁ -C₄ -halogenoalkyl-substitutedalkanediyl, oxoalkanediyl or dioxoalkanediyl having in each case up to 6carbon atoms,

R⁵ represents hydrogen, fluorine, chlorine, bromine or representsrespectively optionally fluorine- and/or chlorine-substituted alkyl oralkoxy having in each case 1 to 4 carbon atoms,

R⁶ represents optionally fluorine- and/or chlorine-substituted alkylhaving 1 to 4 carbon atoms,

R⁷ represents hydrogen or represents respectively optionally fluorine-,chlorine- or C₁ -C₄ -alkoxy-substituted alkyl, alkenyl or alkinyl havingin each case up to 6 carbon atoms, and

R⁸ represents hydrogen or represents respectively optionally fluorine-,chlorine- or C₁ -C₄ -alkoxy-substituted alkyl, alkenyl or alkinyl havingin each case up to 6 carbon atoms.

The invention in particular provides compounds of the formula (I) inwhich

R¹ represents hydrogen, fluorine or chlorine,

R² represents cyano or thiocarbamoyl,

R³ represents hydrogen or represents respectively optionally cyano-,carboxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, n-, i-, s- or t-pentyl, acetyl, n- or i-propyl-carbonyl, n-,i-, s- or t-butyl-carbonyl, propenyl, propenylcarbonyl, butenyl,butenylcarbonyl, pentenyl, pentenylcarbonyl, propinyl, propinylcarbonyl,butinyl, butinylcarbonyl, pentinyl or pentinylcarbonyl,

R³ furthermore represents respectively optionally cyano-, carboxyl-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,methoxy-, ethoxy-, n- or i-propoxy-, acetyl- or propionyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substitutedcyclopropyl, cyclopropylcarbonyl, cyclobutyl, cyclobutylcarbonyl,cyclopentyl, cyclopentylcarbonyl, cyclohexyl, cyclohexylcarbonyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl,

R³ furthermore represents respectively optionally cyano-, carboxyl-,nitro-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-,ethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-,n- or i-propoxycarbonyl-substituted phenylcarbonyl, phenylmethylcarbonylor phenylethylcarbonyl,

R³ furthermore represents respectively optionally cyano-, carboxyl-,carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-,methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, phenyl-,phenoxy- or phenylthio-substituted substituted furylcarbonyl,tetrahydrofurylcarbonyl, thienylcarbonyl, tetrahydrothienylcarbonyl,oxazolylcarbonyl, isoxazolylcarbonyl, thiazolylcarbonyl,oxadiazolylcarbonyl, thiadiazolylcarbonyl, pyrazolylcarbonyl,pyridinylcarbonyl or pyrimidinylcarbonyl,

R⁴ represents hydrogen or represents respectively optionally cyano-,carboxyl-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, n-, i-, s- or t-pentyl, acetyl, n- or i-propyl-carbonyl, n-,i-, s- or t-butyl-carbonyl, propenyl, propenylcarbonyl, butenyl,butenylcarbonyl, pentenyl, pentenylcarbonyl, propinyl, propinylcarbonyl,butinyl, butinylcarbonyl, pentinyl or pentinylcarbonyl,

R⁴ furthermore represents respectively optionally cyano-, carboxyl-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,methoxy-, ethoxy-, n- or i-propoxy-, acetyl- or propionyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substitutedcyclopropyl, cyclopropylcarbonyl, cyclobutyl, cyclobutylcarbonyl,cyclopentyl, cyclopentylcarbonyl, cyclohexyl, cyclohexylcarbonyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl,

R⁴ furthermore represents respectively optionally cyano-, carboxyl-,nitro-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-,ethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-,n- or i-propoxycarbonyl-substituted phenylcarbonyl, phenylmethylcarbonylor phenylethylcarbonyl,

R⁴ furthermore represents respectively optionally cyano-, carboxyl-,carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-,methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, phenyl-,phenoxy- or phenylthio-substituted furylcarbonyl,tetrahydrofurylcarbonyl, thienylcarbonyl, tetrahydrothienylcarbonyl,oxazolylcarbonyl, isoxazolylcarbonyl, thiazolylcarbonyl,oxadiazolylcarbonyl, thiadiazolylcarbonyl, pyrazolylcarbonyl,pyridinylcarbonyl or pyrimidinylcarbonyl, or

R⁴ together with R³ represents respectively optionally fluorine-,chlorine-, methyl- or trifluoromethyl-substituted propane-1,3-diyl(trimethylene), butane-1,4-diyl (tetramethylene), 1-oxo-propane-1,3-diyl, 1-oxo-butane- 1,4-diyl, 1,3-dioxopropane-1,3-diyl or1,4-dioxobutane-1,4-diyl,

R⁵ represents hydrogen, fluorine, chlorine, bromine or methyl,

R⁶ represents methyl, ethyl, difluoromethyl, dichloromethyl,trifluoromethyl, trichloromethyl, chlorodifluoromethyl,fluorodichloromethyl, chloroethyl, fluoroethyl, dichloroethyl,dichloroethyl, chlorofluoroethyl, chlorodifluoroethyl,fluorodichloroethyl, trifluoroethyl, tetrafluoroethyl,chlorotrifluoroethyl or pentafluoroethyl,

R⁷ represents hydrogen or represents respectively optionally fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl ethyl, n- or i-propyl,n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyl, butenyl, propinyl or butinyl, and

R⁸ represents hydrogen or represents respectively optionally fluorine-,chlorine-methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyl, butenyl, propinyl or butinyl.

The radical definitions listed above, whether general or listed inranges of preference, apply not only to the end products of formula (I)but also, correspondingly, to the starting materials and/orintermediates required in each case for the preparation. These radicaldefinitions can be combined as desired with one another, thus includingcombinations between the preferred ranges indicated.

Examples of compounds of the formula (I) according to the invention arelisted in the groups below. ##STR4##

R³ has, for example, the meanings given in the list below: hydrogen,methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- ort-pentyl, acetyl, n- or i-propyl-carbonyl, n-, i-, s- ort-butyl-carbonyl, n-, i-, s- or t-pentyl-carbonyl, difluoroacetyl,trifluoroacetyl, chlorodifluoroacetyl, fluorodichloroacetyl,fluoroprionyl, chloropropionyl, chlorofluoropropionyl,difluoropropionyl, dichloropropionyl, trifluoropropionyl,trichloropropionyl, chlorodifluoropropionyl, tetrafluoropropionyl,chlorotrifluoropropionyl, pentafluoropropionyl, fluorobutyroyl,chlorobutyroyl, difluorobutyroyl, dichlorobutyroyl, trifluorobutyroyl,cyanomethyl, cyanoacetyl, cyanoethyl, cyanopropionyl, cyanopropyl,cyanobutyroyl, carboxymethyl, carboxyethyl, carboxypropyl, carboxybutyl,methoxymethyl, methoxyacetyl, ethoxymethyl, ethoxyacetyl, propoxymethyl,propoxyacetyl, methoxyethyl, methoxypropionyl, ethoxyethyl,propoxyethyl, methoxypropyl, methoxybutyroyl, ethoxypropyl,ethoxybutyroyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,propoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl,propoxycarbonylethyl, methoxycarbonylpropyl, ethoxycarbonylpropyl,1-propen-3-yl (allyl), 3-methyl-1-propen-3-yl, 2-buten-4-yl (crotonyl),1-propin-3-yl (propargyl), 3-methyl-1-propin-3-yl, 2-butin-4-yl,cyclopropyl, cyclopropylcarbonyl, cyanocyclopropyl, carboxycyclopropyl,difluorocyclopropyl, dichlorocyclopropyl, methylcyclopropyl,methoxycarbonylcyclopropyl, ethoxycarbonylcyclopropyl, cyclobutyl,cyclobutylcarbonyl, cyanocyclobutyl, carboxycyclobutyl,difluorocyclobutyl difluorocyclobutylcarbonyl, trifluorocyclobutyl,trifluorocyclobutylcarbonyl, tetrafluorocyclobutyl,tetrafluorocyclobutylcarbonyl, chlorotrifluorocyclobutyl,chlorotrifluorocyclobutylcarbonyl, methylcyclobutyl, cyclopentyl,cyclopentylcarbonyl, cyanocyclopentyl, carboxycyclopentyl,fluorocyclopentyl, chiorocyclopentyl, difluorocyclopentyl,dichlorocyclopentyl, methylcyclopentyl, methoxycarbonylcyclopentyl,ethoxycarbonylcyclopentyl, cyclohexyl, cyclohexylcarbonyl,cyanocyclohexyl, carboxycyclohexyl, fluorocyclohexyl, chlorocyclohexyl,difluorocyclohexyl, dichlorocyclohexyl, methylcyclohexyl,trifluoromethylcyclohexyl, methoxycarbonylcyclohexyl,ethoxycarbonylcyclohexyl, cyclopropylmethyl, difluorocyclopropylmethyl,dichlorocyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyanocyclohexylmethyl, carboxycyclohexylmethyl,fluorocyclohexylmethyl, chlorocyclo-hexylmethyl, methylcyclohexylmethyl,trifluoromethylcyclohexylmethyl, benzoyl, cyanobenzoyl, nitrobenzoyl,fluorobenzoyl, chlorobenzoyl, bromobenzoyl, methylbenzoyl,trifluoromethylbenzoyl, methoxybenzoyl, difluoromethoxybenzoyl,trifluoromethoxybenzoyl, phenylacetyl, furylcarbonyl,tetrahydrofurylcarbonyl, thienylcarbonyl, tetrahydrothienylcarbonyl,oxazolylcarbonyl, isoxazolylcarbonyl, pyridylcarbonyl. ##STR5##

R³ has, for example, the meanings given above for Group 1. ##STR6##

R³ has, for example, the meanings given above for Group 1. ##STR7##

R³ has, for example, the meanings given above for Group 1. ##STR8##

R³ has, for example, the meanings given above for Group 1. ##STR9##

R³ has, for example, the meanings given above for Group 1. ##STR10##

R³ has, for example, the meanings given above for Group 1. ##STR11##

R³ has, for example, the meanings given above for Group 1. ##STR12##

R³ has, for example, the meanings given above for Group 1. ##STR13##

R³ has, for example, the meanings given above for Group 1. ##STR14##

R³ has, for example, the meanings given above for Group 1.

Using, for example,3-amino-4-chlorodifluoromethyl-1-(4-cyano-2-fluoro-5-methylsulphonylamino-phenyl)-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidineand dichloroacetyl chloride as starting materials, the course of thereaction in the process according to the invention can be illustrated bythe following equation: ##STR15##

A general definition of the aminouracils to be used as startingmaterials in the process according to the invention for the preparationof the compounds of the formula (I) is given by the formula (II). In theformula (II), R¹, R², R⁵, R⁶, R⁷ and R⁸ each preferably or in particularhave those meanings which have already been indicated above, inconnection with the description of the compounds of the formula (I) tobe prepared according to the invention, as being preferable or,respectively, particularly preferable for R¹, R², R⁵, R⁶, R⁷ and R⁸ ; Zpreferably represents optionally halogen-substituted C₁ -C₄-alkylsulphonylamino, amino or optionally halogen-substituted C₁ -C₄-alkyl-carbonylamino, in particular methylsulphonylamino,ethylsulphonylamino or trifluoroacetylamino.

The starting materials of the formula (II) are known and/or can beprepared by known processes (cf. EP 408382, EP 648749).

A general definition of the alkylating or acylating agents further to beused as starting materials in the process according to the invention forthe preparation of the compounds of the formula (I) is given by formulae(III), (IV), (V) and (VI). In these formulae, R³ and R⁴ each preferablyor in particular have those meanings which have already been indicatedabove, in connection with the description of the compounds of theformula (I) to be prepared according to the invention, as beingpreferable or, respectively, particularly preferable for R³ and R⁴.

The starting materials of the formulae (III), (IV), (V) and (VI) areknown chemicals for synthesis.

The process according to the invention for preparing compounds of theformula (I) is preferably carried out in the presence of a suitablereaction auxiliary. Suitable reaction auxiliaries are generally thecustomary inorganic or organic bases or acid acceptors. These includepreferably alkali metal or alkaline earth metal acetates, amides,carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as,for example, sodium acetate, potassium acetate or calcium acetate,lithium amide, sodium amide, potassium amide or calcium amide, sodiumcarbonate, potassium carbonate or calcium carbonate, sodium bicarbonate,potassium bicarbonate, or calcium bicarbonate, lithium hydride, sodiumhydride, potassium hydride or calcium hydride, lithium hydroxide, sodiumhydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide orpotassium methoxide, sodium ethoxide or potassium ethoxide, sodium n- ori-propoxide or potassium n- or i-propoxide, sodium n-, i-, s- ort-butoxide or potassium n-, i-, s- or t-butoxide; furthermore also basicorganic nitrogen compounds, such as, for example trimethylamine,triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine,N,N-dimethyl-cyclohexylamine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine,4-dimethylamino-pyridine, N-methyl-piperidine,1,4-diazabicyclo[2,2,2]-octane (DABCO),1,5-diazabicyclo[4,3,0]-non-5-ene (DBN), and 1,8diazabicyclo[5,4,0]-undec-7-ene (DBU).

The process according to the invention for preparing compounds of theformula (I) is preferably carried out in the presence of a diluent.Suitable diluents are in general the customary organic solvents. Theseinclude preferably aliphatic, alicyclic and aromatic, optionallyhalogenated hydrocarbons, such as, for example, pentane, hexane,heptane, petroleum ether, ligroin, benzine, benzene, toluene, xylene,chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane,dichloromethane (methylene chloride), trichloromethane (chloroform) orcarbon tetrachloride, dialkyl ethers, such as, for example, diethylether, diisopropyl ether, methyl t-butyl ether (MTBE), ethyl t-butylether, methyl t-pentyl ether (TAME), ethyl t-pentyl ether,tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl ether orethylene glycol diethyl ether, diethylene glycol dimethyl ether ordiethylene glycol diethyl ether; dialkyl ketones, such as, for example,acetone, butanone, (methyl ethyl ketone), methyl i-propyl ketone ormethyl i-butyl ketone, nitriles, such as, for example, acetonitrile,propionitrile, butyronitrile or benzonitrile; amides, such as, forexample, N,N-dimethyl-formamide (DMF), N,N-dimethyl-acetamide,N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphorictriamide; esters, such as, for example, methyl acetate, ethyl acetate,n- or i-propyl acetate, n-, i- or s-butyl acetate; sulphoxides, such as,for example, dimethylsulphoxide; alcanols, such as, for example,methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethyleneglycol monomethyl ether or ethylene glycol monoethyl ether, diethyleneglycol monomethyl ether or diethylene glycol monoethyl ether; theirmixtures with water or pure water.

In the practice of the process according to the invention, the reactiontemperatures can be varied over a relatively wide range. Generally, thereaction is carried out at temperatures between 0° C. and 150° C.,preferably between 10° C. and 120° C.

The process according to the invention is generally carried out atatmospheric pressure. However, it is also possible to carry out theprocess according to the invention under elevated or reducedpressure--generally between 0.1 bar and 10 bar.

In the practice of the process according to the invention, the startingmaterials are generally employed in approximately equimolar amounts.However, it is also possible to use a relatively large excess of one ofthe components. The reaction is generally carried out in a suitablediluent in the presence of a reaction auxiliary, and the reactionmixture is generally stirred for several hours at the temperaturerequired. Work-up is carried out by conventional methods (cf. thepreparation examples).

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed-killers.By weeds in the broadest sense, there are to be understood all plantswhich grow in locations where they are not wanted. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria,Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio,Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum,Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala,Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis,Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal control of weeds, for example on industrial terrain and railwaytracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for controlling weeds inperennial cultures, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, inlawns, turf and pasture-land, and for the selective control of weeds inannual cultures.

The compounds of the formula (I) according to the invention are suitablein particular for selectively controlling monocotyledonous anddicotyledonous weeds in monocotyledonous cultures, both pre-emergenceand post-emergence.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspo-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates, suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,as well as synthetic granules of inorganic and organic meals, andgranules of organic material such as sawdust, coconut shells, maize cobsand tobacco stalks; suitable emulsifying and/or foam-forming agents are:for example nonionic and anionic emulsifiers, such as polyoxyethylenefatty acid esters, polyoxyethylene fatty alcohol ethers, for examplealkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,arylsulphonates as well as protein hydrolysates; suitable dispersingagents are: for example lignin-sulphite waste liquors andmethylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Further additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyes, such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in the form of their formulations, can also be used asmixtures with known herbicides, finished formulations or tank mixesbeing possible.

Possible components for the mixtures are known herbicides, for exampleanilides, such as diflufenican and propanil; arylcarboxylic acids, suchas dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids,such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic esters, such as diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones, such as chloridazon and norflurazon;carbamates, such as chlorpropham, desmedipham, phenmedipham and propham;chloroacetanilides, such as alachlor, acetochlor, butachlor,metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines,such as oryzalin, pendimethalin and trifluralin; diphenyl ethers, suchas acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofenand oxyfluorfen; ureas, such as chlorotoluron, diuron, fluometuron,isoproturon, linuron and methabenzthiazuron; hydroxylamines, such asalloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim;imidazolinones, such as imazethapyr, imazamethabenz, imazapyr andimazaquin; nitriles, such as bromoxynil, dichlobenil and ioxynil;oxyacetamides, such as mefenacet; sulphonylureas, such as amidosulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl;thiocarbamates, such as butylate, cycloate, diallate, EPTC, esprocarb,molinate, prosulfocarb, thiobencarb and triallate; triazines, such asatrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine;triazinones, such as hexazinone, metamitron and metribuzin; and others,such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone,clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone,glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac,sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES Example 1 ##STR16##

A mixture of 2.1 g (5 mmol) of3-amino-1-(4-cyano-2-fluoro-5-ethylsulphonyl-amino-phenyl)-5-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidine,1.1 g (5.5 mmol) of trifluoroacetic anhydride, 1 ml of triethylamine and20 ml of acetonitrile is heated under reflux for 30 hours and thenconcentrated using water pump vacuum. The residue is taken up on ethylacetate, washed with 1N hydrochloric acid, dried with sodium sulphateand filtered. The filtrate is concentrated using water pump vacuum, andthe crude product which is obtained as residue is purified by columnchromatography (silica gel, chloroform/ethyl acetate, Vol. 1:1).

0.8 g (38% of theory) of3-amino-1-(4-cyano-2-fluoro-5-trifluoroacetyl-amino-phenyl)-5-trifluoromethyl-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidineis obtained.

¹ H NMR (dimethyl sulphoxide-D6, δ): 6.47 ppm.

Similar to the method of Example 1 and according to the generaldescription of the process according to the invention, for example thecompounds of the formula (I) listed in Table 1 below can also beprepared. ##STR17##

                                      TABLE 1                                     __________________________________________________________________________    Examples of compounds of the formula (I)                                      Ex.                              physical                                       No. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7 R.sup.8         __________________________________________________________________________                                     data                                          2 F CN  H   H         H CF.sub.3                                                                         H  H                                                 3 F CN H CH.sub.3 H CF.sub.3 H H                                              4 F CN CH.sub.3 CH.sub.3 H CF.sub.3 H H                                       5 F CN CH.sub.3 C.sub.3 H.sub.7 -i H CF.sub.3 H H                             6 F CN H C.sub.2 H.sub.5 H CF.sub.3 H H                                       7 F CN H C.sub.3 H.sub.7 -n H CF.sub.3 H H                                    8 F CN H C.sub.3 H.sub.7 -i H CF.sub.3 H H                                  9 F CN  --(CH.sub.2).sub.4 --                                                                       H CF.sub.3                                                                         H  H                                              10 F CN  H   COCF.sub.3                                                                              H CF.sub.3                                                                         H  H                                                11 F CN H COC.sub.2 F.sub.5 H CF.sub.3 H H                                    12 F CN H COCH.sub.3 H CF.sub.3 H H                                           13 F CN COCH.sub.3 COCH.sub.3 H CF.sub.3 H H                                14 F CN  --CO--CH.sub.2 CH.sub.2 --CO--                                                              H CF.sub.3                                                                         H  H                                              15 F CN  H   COC.sub.2 H.sub.5                                                                       H CF.sub.3                                                                         H  H                                                 - 16 F CN H                                                                                                 H CF.sub.3 H H                                  - 17 F CN H                                                                                                 H CF.sub.3 H H                                  - 18 F CN H                                                                                                 H CF.sub.3 H H                                  - 19 F CN H COC.sub.4 H.sub.9 -t H CF.sub.3 H H                              20 F CN H COC.sub.3 H.sub.7 -i H CF.sub.3 H H                                 21 F CN CH.sub.3 COCH.sub.3 H CF.sub.3 H H                                    22 F CN C.sub.2 H.sub.5 COC.sub.4 H.sub.9 -n H CF.sub.3 H H                   23 F CN CH.sub.3 COCF.sub.3 H CF.sub.3 H H                                     - 24 F CN COCH.sub.3                                                                                        H CF.sub.3 H H                                  - 25 F CN H CH.sub.2 COOCH.sub.3 H CF.sub.3 H H                              26 F CN CH.sub.3 CH.sub.2 COOCH.sub.3 H CF.sub.3 H H                          27 F CN COCH.sub.3 CH.sub.2 CN H CF.sub.3 H H                                 28 F CN H CH.sub.2 CH.sub.2 CN H CF.sub.3 H H                                 29 F CSNH.sub.2 H COCF.sub.3 H CF.sub.3 H H                                   30 F CN H COCHCl.sub.2 H CF.sub.3 H H                                         31 F CN                                                                                                        H CF21##                                                                    .sub.3 H H                                      - 32 F CN                                                                                                     H CF.sub.3 H H                                -                                                                          33 F CN  H   CH.sub.3  H CF.sub.3                                                                         CH.sub.3                                                                         H                                                34 F CSNH.sub.2 H CH.sub.3 H CF.sub.3 CH.sub.3 H                               - 35 F CN H                                                                                                 H CF.sub.3 H H                               __________________________________________________________________________

USE EXAMPLES Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours,the soil is watered with the preparation of the active compound.Advantageously, the amount of water per unit area is kept constant. Theactive compound concentration in the preparation is not important, onlythe active compound application rate per unit area being decisive.

After three weeks, the degree of damage to the plants is rated in %damage in comparison with the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, a very strong activity against weeds such as Setaria(100%), Sorghum (90%), Abutilon (100%), Galium (100%), Matricaria (100%)and Polygonum (100%) is shown, for example, by the compound ofPreparation Example 1 at an application rate of 30 g/ha, combined withvery good tolerance by crops, such as, for example, maize (0%).

Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen so that the amounts ofactive compound desired are applied in 1000 l/ha.

After three weeks, the degree of damage to the plants is rated in %damage in comparison with the development of the untreated control.

The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, a very strong activity against weeds such as Echinochloa(100%), Abutilon (100%), Datura (100%), Ipomoea (100%) and Viola (100%)is shown, for example, by the compound of Preparation Example 1 at anapplication rate of 30 g/ha, combined with very good tolerance by crops,such as, for example, wheat (0%).

We claim:
 1. Substituted aminouracils of the formula (I) ##STR24## inwhich the substituents R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ represent thefollowing:

    ______________________________________                                        R.sup.1                                                                           R.sup.2 R.sup.3 R.sup.4     R.sup.5                                                                           R.sup.6                                                                            R.sup.7                                                                            R.sup.8                         ______________________________________                                        F   CN      H       H           H   CF.sub.3                                                                           H    H                                 F CN H CH.sub.3 H CF.sub.3 H H                                                F CN CH.sub.3 CH.sub.3 H CF.sub.3 H H                                         F CN CH.sub.3 C.sub.3 H.sub.7 -i H CF.sub.3 H H                               F CN H C.sub.2 H.sub.5 H CF.sub.3 H H                                         F CN H C.sub.3 H.sub.7 -n H CF.sub.3 H H                                      F CN H C.sub.3 H.sub.7 -i H CF.sub.3 H H                                    F   CN      --(CH.sub.2).sub.4 --                                                                           H   CF.sub.3                                                                           H    H                                 F   CN      H       COCF.sub.3  H   CF.sub.3                                                                           H    H                                 F CN H COC.sub.2 F.sub.5 H CF.sub.3 H H                                       F CN H COCH.sub.3 H CF.sub.3 H H                                              F CN COCH.sub.3 COCH.sub.3 H CF.sub.3 H H                                   F   CN      --CO--CH.sub.2 CH.sub.2 --CO--                                                                  H   CF.sub.3                                                                           H    H                                 F   CN      H       COC.sub.2 H.sub.5                                                                         H   CF.sub.3                                                                           H    H                                  - F CN H                                                                                                                   H CF.sub.3 H H                   - F CN H                                                                                                                   H CF.sub.3 H H                   - F CN H                                                                                                                   H CF.sub.3 H H                   - F CN H COC.sub.4 H.sub.9 -t H CF.sub.3 H H                                 F CN H COC.sub.3 H.sub.7 -i H CF.sub.3 H H                                    F CN CH.sub.3 COCH.sub.3 H CF.sub.3 H H                                       F CN C.sub.2 H.sub.5 COC.sub.4 H.sub.9 -n H CF.sub.3 H H                      F CN CH.sub.3 COCF.sub.3 H CF.sub.3 H H                                        - F CN COCH.sub.3                                                                                                          H CF.sub.3 H H                   - F CN H CH.sub.2 COOCH.sub.3 H CF.sub.3 H H                                 F CN CH.sub.3 CH.sub.2 COOCH.sub.3 H CF.sub.3 H H                             F CN COCH.sub.3 CH.sub.2 CN H CF.sub.3 H H                                    F CN H CH.sub.2 CH.sub.2 CN H CF.sub.3 H H                                    F CSNH.sub.2 H COCF.sub.3 H CF.sub.3 H H                                      F CN H COCHCl.sub.2 H CF.sub.3 H H                                            F CN                                                                                                                      H CF29##                                                                    .sub.3 H H                           - F CN                                                                                                                   H CF.sub.3 H H                     -                                                                          F   CN      H       CH.sub.3    H   CF.sub.3                                                                           CH.sub.3                                                                           H                                 F CSNH.sub.2 H CH.sub.3 H CF.sub.3 CH.sub.3 H                                  - F CN H                                                                                                                   H CF.sub.3 H H                ______________________________________                                    


2. A substituted aminouracil of the formula ##STR32##
 3. Herbicidalcompositions, comprising at least one substituted aminouracil of theformula (I) according to claim 1 and an extender or surface activesubstance.
 4. A method for controlling undesirable plants, comprisingadministering to such plants or to a locus from which it is desired toexclude such plants an herbicically effective amount of substitutedaminouracils of the general formula (I) according to claim 1.